Careers aren’t linear. They’re Loops.

We should all know by now that careers are not a nice path with predictable, step-by-step rules.

There is no one “right” path or “safe” path. Careers are full of delightful detours and unexpected obstacles (like layoffs).

But knowing this doesn’t make it any less scary or less of a struggle to navigate.

You can’t pick the right path for a future that hasn’t been invented yet. But you can build the skills and confidence to design your path, no matter what the future holds.

The key to career design is the power of small experiments.

Small experiments help you move quickly, build momentum, and invite the world to help you discover your next move and make it happen.

We call these small experiments Loops as an invitation to embrace the “loopy” career reality and make it work to your advantage.

Looping Origins

For the last decade, I have used problem solving practices like design thinking, lean startup, thinking wrong, and effectual thinking to solve challenges when the path is unclear.

When it comes to unclear career paths, these practices bring a lot of the right mindset to the table, but have been thoughtfully refined for a unique purpose; tackling wicked problems, overcoming startup friction, and inspiring bold thinking needed for innovation.

Career design has it’s own unique challenges.

So I started crafting, testing, and iterating on a new toolkit specific to career design and with a very low learning curve.

This year, I’m bringing Looping Method out a long incubation.

By design, Looping Method is similar to tools like design thinking in the sense that no one owns it. I am an author and, with time, there will be many authors. You can use it without license and even for profit.

A Brief Introduction To Making A Loop

Looping Method is a framework for designing sequential small experiments to discover what you want and craft smart moves to make it happen.

The guiding pillars:

  1. Getting started is more important than being right.
  2. Come bearing gifts and the world will give you gifts in return.
  3. We know more than me. (invite others to close your knowledge gaps)
  4. Don’t be boring, nobody wants to connect with boring.

These pillars capture the importance of following your curiosity (rather than knowing your passion), cultivating a growth mindset, building your imagination and maker muscles, and observing jobs to be done (learning to create value).

All together, these practices dramatically boost your confidence.

Loops are meant to have a low learning curve. You have a few guiding pillars and four short steps.

That said, there is more to Looping than this brief overview. There are drills and frameworks to guide each step in a way that helps us see what is possible and avoid getting stuck.

The Four Steps

  1. Clarify
  2. Create
  3. Connect
  4. Reflect, Refine, Restart

Step 1. Clarify

To start a Loop, you have to first Clarify the challenge you want to solve for.

This step includes unique exercises designed to reveal and reflect on what you need and what obstacles are in the way.

You are not trying to solve for everything all at once. Looping is a continual practice. Finishing one Loop gives you insights to propel you into the next Loop, like a roller coaster, to build on your new momentum.

Clarifying is about getting specific about what you need or what obstacle is in your way.

For example, “get a new job” is too broad of a challenge. What kind of role? What industry? What career gaps are in the way?

Let’s say you are interested in UX careers. Someone considering a new path might ask:

How might I learn if UX roles are a good fit for me and the impact I want to have through my work?

The “impact” here could then be defined to better focus the possible solutions in the next step.

Another question might involve UX skills:

How might I learn about the UX skills I need to develop so that I can transition into design roles?

Let’s say you have direction, skills and some target companies picked out. You might ask:

How might I get a foot in the door with the company I’m excited about so that I can position myself to join the team, even though they don’t have open positions?

Step 2. Create

The Create step is about generating ways you might solve your challenge in Step 1, and then pick one solution to pursue.

Create can be many things; digital, tactile, or experiential.

  • You might Create a convening by hosting a dinner party.
  • You might Create a job shadow opportunity and document what you learned.
  • You might Create work for a potential employer by doing the job you wish you had.

Creating is critical. It is how you leave a trail of work for others to follow.

To make sure we start quickly and avoid losing momentum, we use the Smallify test to ask how we might reduce the effort and time to complete the Create step.

For example, writing a book can Smallify to writing a short blog post.

Step 3. Connect

What you Create must Connect with real people other than your best friend.

Often times, connecting with people is inherent to what you Create. Other times you will have to challenge yourself to not work in isolation.

This step is crucial because we know more than me → you have limited knowledge and connecting helps you close it.

Additionally, connecting is the invitation for serendipity. When you leave a trail of what you created, you invite serendipity. Now your career journey shifts to inbound opportunities.

Step 4. Reflect

A completed Loop will give you new insights to inform your next moves.

Reflect on what you learned to refine your challenge and then restart the Looping process.

A Loop can be completed in under a week giving you new insights, new connections, and momentum to propel your career. You can’t say the same for throwing resumes into the application black hole.


You can’t think your way into a great career.

Small experiments are the key to getting out of your head and inviting the world to help you discover your next move and make it happen.

I know this is a short overview and there is much more to share about Looping. The best way to learn is through example (like this and this) and practice. To help you do both, I’ve set up a community to learn and take action with a community to lean on for support.

For employers and college career offices, I’m putting together a Master Class to help you learn and apply Looping with your employees and students.

Take a look at a full day career workshop.

Connect with me on LinkedIn to chat about collaborating :)